Method and means for detecting polyhydroxyl compounds

• US 5,512,246 A
• Filed: 11/17/1993
• Issued: 04/30/1996
• Est. Priority Date: 09/21/1989
• Status: Expired due to Term

• Current Assignee: Medtronic Minimed Incorporated (Medtronic Plc)
• Original Assignee: Anthony P. Russell
• Inventors: Zepp, Charles W., Russell, Anthony P.
• Primary Examiner(s): Ramsuer, Robert W.
• Assistant Examiner(s): POWERS, FIONA
• Application Number:
  US08/153,763
• Time in Patent Office: 895 Days
• Field of Search: 422/82.09, 422/55, 422/57, 534/726
• US Class Current: 422/400
• CPC Class Codes: G01N 33/521 Single-layer analytical elements
• CPC Class Codes: G01N 33/523 the element being adapted for a specific analyte
• CPC Class Codes: G01N 33/66 involving blood sugars, e.g. galactose

Abstract

Methods and compositions for detecting and measuring the concentration in solution of polyhydroxyl compounds, such as sugars. The invention makes use of certain dye compositions that, when linked to a derivative of boronic acid (or boronate ion), arsenious acid (or arsenite ion), or germanic acid (or germanate ion), exhibit quantitative responses to the presence of polyhydroxyl species.

Claims

1. A bound dye compound that exhibits quantitative sensitivity to carbohydrate species, the compound comprising a binding moiety selected from the group consisting of boronic acid, boronate ion, arsenious acid, arsenite ion, telluric acid, tellurate ion, germanic acid and germanate ion, covalently linked to a dye group such that the compound exhibits the properties of a dye and wherein binding of said compound to a carbohydrate results in quantitative alteration of the dye properties of said molecule in response to the concentration of said carbohydrate species, and further wherein said linked compound is covalently bound to a support.

2. The dye compound of claim 1 wherein said binding moiety is selected from the group consisting of aminophenylboronic acid, aminophenylboronate, aminophenylarsenious acid, aminophenylarsenite, aminophenyltelluric acid, aminophenyltellurate, aminophenylgermanic acid and aminophenylgermanate.

3. The dye compound of claim 1 wherein the dye group is an azo species.

4. The dye compound of claim 1 wherein the dye group is a triphenylmethane species.

5. A dye compound that exhibits quantitative sensitivity to carbohydrate species, the compound being prepared by diazotizing an aryl compound selected from the group consisting of aminophenylboronic acid, aminophenylboronate, aminophenylarsenious acid, aminophenylarsenite, aminophenyltelluric acid, aminophenyltellurate, aminophenylgermanic acid and aminophenylgermanate, and coupling said diazotized aryl compound to an electron donating species, such that the compound formed thereby exhibits the properties of a dye and wherein binding of said compound to a carbohydrate results in quantitative alteration of the dye properties of said compound in response to the concentration of said carbohydrate species, and further wherein said linked compound is covalently bound to a support.

6. The dye compound of claim 5 wherein said electron donating species is selected from the group consisting of aminophenylboronic acid, aminophenylboronate, aminophenylarsenious acid, aminophenylarsenite, aminophenyltelluric acid, aminophenyltellurate, aminophenylgermanic acid, aminophenylgermanate and aminated polystyrene polymers and copolymers.